Part of the Ph. D. thesis of T. L. Sommerfeld, Dissertation No. 10842, ETH Zürich, 1994.
Synthesis of ψ[SCH2]-, ψ[SOCH2]-, and ψ[SO2CH2]-Peptide Isosters†
Article first published online: 22 DEC 2003
Copyright © 1995 by VCH Verlagsgesellschaft mbH, Germany
Angewandte Chemie International Edition in English
Volume 34, Issue 5, pages 553–554, March 20, 1995
How to Cite
Sommerfeld, T. and Seebach, D. (1995), Synthesis of ψ[SCH2]-, ψ[SOCH2]-, and ψ[SO2CH2]-Peptide Isosters. Angew. Chem. Int. Ed. Engl., 34: 553–554. doi: 10.1002/anie.199505531
- Issue published online: 22 DEC 2003
- Article first published online: 22 DEC 2003
- Manuscript Received: 20 SEP 1994
- peptide isosteres;
- sulfur compounds
Novel peptide analogues 2 containing -SOn-CH2- instead of -CO-NH- (n = 0, 1, 2) may be prepared as single stereoisomers from amino acids and peptides 1 by electrolysis, reaction with 3-mercaptocarboxylic acids, and oxidation. The stability of 2 (especially under basic conditions) decreases with increasing oxidation state at sulfur and with increasing donor ability of the nitrogen atom.